Structure-Antioxidant-Antiproliferative Activity Relationships of Natural C7 and C7-C8 Hydroxylated Flavones and Flavanones

• Published in: Antioxidants Vol. 8; no. 7; p. 210
• Main Authors: Sordon, Sandra, Popłoński, Jarosław, Milczarek, Magdalena, Stachowicz, Martyna, Tronina, Tomasz, Kucharska, Alicja Z, Wietrzyk, Joanna, Huszcza, Ewa
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 07.07.2019; MDPI
• Subjects: Acids; anticancer activity; antioxidant activity; Antioxidants; Biotransformation; Breast cancer; Breast carcinoma; Cancer; Catechol; catechol moiety; Cell cycle; Chemical synthesis; Colon cancer; Doxorubicin; Endothelial cells; flavanones; Flavones; Flavonoids; Hesperidin; hydroxylation; Microvasculature; Myelomonocytic leukemia; Naringenin; NMR; Nuclear magnetic resonance; Prostate cancer; Spectrum analysis; Tumor cell lines; United States > US; flavones; anticancer activity; hydroxylation; antioxidant activity; catechol moiety; flavanones
• ISSN: 2076-3921; 2076-3921
• DOI: 10.3390/antiox8070210

Common food flavonoids: chrysin, apigenin, luteolin, diosmetin, pinocembrin, naringenin, eriodictyol, hesperetin, and their analogues with an additional hydroxyl group at the C-8 position obtained via biotransformation were tested for antioxidant activity using the ABTS, DPPH, and ferric ion reducing antioxidant power (FRAP) methods. They were also tested for antiproliferative activity against selected human cancer cell lines-MV-4-11 (biphenotypic B myelomonocytic leukemia), MCF7 (breast carcinoma), LoVo (colon cancer), LoVo/DX (colon cancer doxorubicin resistant), and DU 145 (prostate cancer)-and two normal human cell lines-MCF 10A (breast cells) and HLMEC (lung microvascular endothelial cells). Flavonoids with a C7-C8 catechol moiety indicated much higher antioxidant activity compared with the C7 hydroxy analogues. However, because they were unstable under the assay conditions, they did not show antiproliferative activity or it was very low.